Total synthesis of a thymidine 2-deoxypolyoxin C analogue

被引：25

作者：

Dehoux, C ^{[1
]}

Fontaine, E ^{[1
]}

Escudier, JM ^{[1
]}

Baltas, M ^{[1
]}

Gorrichon, L ^{[1
]}

机构：

[1] Universite Paul Sabatier, Lab Synthese & Physicochim Organ, CNRS, ESA 5068, F-31062 Toulouse 4, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 08期

关键词：

D O I：

10.1021/jo972116s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the thymidine 2-deoxypolyoxin C analogue 10 from a noncarbohydrate precursor was achieved in 10 steps and 9% yield starting from a chiral gamma,delta-epoxy-beta-hydroxy ester 11 readily available from cis-2-butene-1,4-diol, The main steps concern the stereo-and regioselective opening of the epoxide ring by an azide anion, the stereoselective introduction of the thymine base, and the transformation of the primary alcohol to the acid functionality of the final product. Two other approaches have also been investigated.

引用

页码：2601 / 2608

页数：8

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